Sulfuric Acid → Methyl 7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1640113노트

반응식

HRID 1640113 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:14]([O:16][CH3:17])=[O:15])[C:10]2=O)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[H][H]>[Pd].CC(O)=O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)=[CH:5][CH:4]=1

참가 물질

7

반응물 3

HCID 1118Sulfuric AcidHCID 14722817Methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 13058284Methyl 7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate수율 71%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

A slurry of methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (6.0 g, 26 mmol) and 10% palladium on carbon (100 mg) in AcOH (120 mL), and concentrated sulfuric acid (780 μL) was allowed to stir under 30 psi of hydrogen for 2.5 h. The reaction mixture was diluted with chloroform, and filtered through Celite. The filtrate was washed with water (5×), dried over Na2SO4 and evaporated. The residue was purified by filtration through a pad of silica, to give methyl 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylate as an oil (4.03 g, 71%). 1H NMR (300 MHz, CD3OD): δ 6.94 (d, 1H), 6.67-6.62 (m, 2H), 3.72 (s, 3H), 3.69 (s, 3H), 2.94-2.91 (m, 2H), 2.78-2.70 (m, 3H), and 2.18-2.09 (m, 1H), and 1.86-1.73 (m, 1H).

후처리

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with water (5×)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. filtrationThe residue was purified by filtration through a pad of silica

출처 및 근거

ORD 기록
ord-0db14d2d357b47daa9112ca49aea7d90
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

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